Sodium Chloride → N-(3-amino-5-trifluoromethyl-2-pyridyl)ethanesulfonamide

HRID 2396457Notes

Reaction equation

HRID 2396457 reaction equation
S(S([O-])=O)([O-])=O.[Na+].[Na+].[N+:9]([C:12]1[C:13]([NH:22][S:23]([CH2:26][CH3:27])(=[O:25])=[O:24])=[N:14][CH:15]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:17]=1)([O-])=O.[Cl-].[Na+]>O.O1CCCC1>[NH2:9][C:12]1[C:13]([NH:22][S:23]([CH2:26][CH3:27])(=[O:25])=[O:24])=[N:14][CH:15]=[C:16]([C:18]([F:21])([F:19])[F:20])[CH:17]=1

Participants

6

Reactant 3

HCID 5234Sodium ChlorideHCID 24489Sodium DithioniteHCID 10851681N-(3-nitro-5-trifluoromethyl-2-pyridyl)ethanesulfonamide

Product 1

HCID 10730665N-(3-amino-5-trifluoromethyl-2-pyridyl)ethanesulfonamideYield 93.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

An alternative process will be described. To a solution prepared by dissolving 34.9 g of sodium hydrosulfite in 400 ml of water, a solution prepared by dissolving 5.0 g of N-(3-nitro-5-trifluoromethyl-2-pyridyl)ethanesulfonamide in 80 ml of tetrahydrofuran, was dropwise added at room temperature. After completion of the dropwise addition, the mixture was reacted for further 3 hours. After completion of the reaction, sodium chloride was added until the tetrahydrofuran layer was separated. The separated tetrahydrofuran layer was dried, and tetrahydrofuran was distilled off under reduced pressure to obtain 4.2 g of N-(3-amino-5-trifluoromethyl-2-pyridyl)ethanesulfonamide.

Workup

  1. customTo a solution prepared
  2. customa solution prepared
  3. additionwas dropwise added at room temperature
  4. additionAfter completion of the dropwise addition
  5. customthe mixture was reacted for further 3 hours
  6. customwas separated
  7. dry with materialThe separated tetrahydrofuran layer was dried
  8. distillationtetrahydrofuran was distilled off under reduced pressure

Sources & evidence

ORD record
ord-1ff7e2879ccb448da54726fa245592e1
Source dataset
uspto-grants-1996_02
Patent number
US05492908

Reaction notes

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